We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Montalcino, Italy

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 121 Rentals in Montalcino
    loading...
    Travellers to Montalcino are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    Sort by
    From
    $163
    / Night
    Payment Protection
    View Details
    1 / 11
    1 Bedroom / Sleeps 2
    Overview Make Enquiry
    From
    $163
    / Night
    Payment Protection
    View Details
    1 / 11
    1 Bedroom / Sleeps 2
    Overview Make Enquiry
    From
    $218
    / Night
    Payment Protection
    View Details
    1 / 11
    1 Bedroom / Sleeps 3
    Overview Make Enquiry
    From
    $102
    / Night
    Payment Protection
    View Details
    1 / 11
    1 Bedroom / Sleeps 1
    Overview Make Enquiry
    From
    $4,255
    / Week
    View Details
    1 / 60
    5 of 5 stars (7) Excellent
    6 Bedrooms / 7 Bathrooms / Sleeps 12
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    PRIVATE STRUCTURE. The villa is situated on an isolated hill, surrounded by the green Tuscan countryside, in the heart of the Val d'Orcia between San Quirico and Montalcino. Il Giardiniello is an old Leopoldino villa of unique architectural style, with the original structure dating to the 16th... View all property information
    Make Enquiry
    From
    $109
    / Night
    Payment Protection
    View Details
    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    From
    $218
    / Night
    Payment Protection
    View Details
    1 / 2
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    From
    $163
    / Night
    Payment Protection
    View Details
    1 / 9
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The Chalet has been constructed on two levels, on the top floor there is one kingsize bedroom with one bathroom while on the bottom floor there is a lounge area with sofas where you can relax. It is situated inside The Convento dei Cappuccini property, a centuries-old wood with cypresses and fruit... View all property information
    Make Enquiry
    From
    $128
    / Night
    Payment Protection
    View Details
    1 / 84
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    2-room apartment 60 m2, on the upper ground floor, spacious, renovated, beautiful and tasteful furnishings: living/dining room with satellite TV. 1 double bedroom. Kitchenette (oven, X ceramic glass hob hotplates). Shower/bidet/WC. Air-conditioning (extra). Small terrace. Terrace furniture.... View all property information
    Make Enquiry
    From
    $223
    / Night
    View Details
    1 / 12
    5 of 5 stars (4) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    The Villa La Scuola Vecchia, in the hamlet of Vergelle in Tuscany, is part of an old school building that was fully renovated in 2008 and is a large 3 bedroom property, which provides comfortable accommodation for up to 8 people. It is a beautiful bright and spacious house spread over three... View all property information
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $128
    / Night
    Payment Protection
    View Details
    1 / 64
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    2-room apartment 60 m2, on the upper ground floor, spacious, renovated, beautiful and tasteful furnishings: living/dining room with satellite TV. 1 double bedroom. Kitchenette (oven, X ceramic glass hob hotplates). Shower/bidet/WC. Air-conditioning (extra). Small terrace. Terrace furniture.... View all property information
    Make Enquiry
    From
    $851
    / Night
    View Details
    1 / 12
    4 of 5 stars (2) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    If you’re an oenophile who dreams of a Tuscan vacation, villa Le Vigne is for you. Located on a working wine estate near Montalcino, the renovated 18th-century stone farmhouse is surrounded by vineyards, and guests can arrange to tour the on-site wine cellar and have a private tasting. If you’re... View all property information
    Make Enquiry
    From
    $11,920
    / Week
    View Details
    1 / 14
    4 of 5 stars (2) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Friends and family alike will appreciate the seamless combination of this contemporary style with rustic Italian beauty. Renting this farmhouse accommodation also means having panoramic views of the countryside and surrounding vineyards, and a variety of options for lovers of nature, architecture,... View all property information
    Make Enquiry
    From
    $9,462
    / Week
    View Details
    1 / 14
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    La Giocosa is located in the most desirable region south of Siena, in the Val d'Orcia, an enchanting and miraculously unspoilt valley in southern Tuscany, listed as UNESCO world heritage in 2004. This beautiful country house is located just 10 km from the historical centre of Montalcino. Set on a... View all property information
    Make Enquiry
    From
    $5,638
    / Week
    View Details
    1 / 32
    Castelnuovo dell'Abate
    14 Bedrooms / 11 Bathrooms / Sleeps 28
    Overview Make Enquiry
    Amenities & Details
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Villa Romanica is a beautiful house near Montalcino, set in an area with a gorgeous view of the countryside. The home has spectacular character and charm, styled in a rustic fashion with quality furnishings throughout. There is a remarkable garden and walking path behind the villa with tables and... View all property information
    Make Enquiry
    From
    $4,014
    / Week
    View Details
    1 / 20
    5 of 5 stars (3) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Villa Brunello is as close to the universal dream of a perfect Tuscan country retreat as can be found! Set amongst a haven of natural tranquility and beauty, surrounded by twenty... View all property information
    Make Enquiry
    From
    $6,399
    / Week
    View Details
    1 / 24
    5 of 5 stars (1) Excellent
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    About this property
    This spacious, stylishly furnished villa is set in extensive grounds, which offer a choice of venues for outdoor relaxation and dining. It is tucked away in a very secluded spot, amid gently rolling wooded hills. From its privileged hillside vantage point, it looks out across a valley covered in... View all property information
    Make Enquiry
    From
    $2,953
    / Week
    View Details
    1 / 21
    4.5 of 5 stars (34) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Reviews (34) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This beautiful villa for rent in Tuscany is in a great location - within walking distance of the town of Montalcino and is an ideal starting point for excursions around southern Tuscany. You'll love exploring Siena and the other surrounding towns, but you'll also want to spend plenty of time at... View all property information
    Make Enquiry
    From
    $1,402
    / Week
    View Details
    1 / 25
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Mountain Views
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    'Vivo d'Orcia is not a place, it is a way of life...' The Castle of Vivo d'Orcia lies in the widespread Orcia valley in southern Tuscany, 2 hours from Florence, 1 hour from Siena, close to such cultural jewels as Pienza, Montalcino and Montepulciano, to name but a few. The hamlet lies at an... View all property information
    Make Enquiry
    From
    $8,782
    / Week
    View Details
    1 / 22
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amiata is a carefully and tastefully renovated country villa set in the most desirable location in the beautiful Val d’Orcia.  Guests are accommodated in four queen bedded rooms. There are four bathrooms.  The villa has been recently updated with every possible modern convenience.  Amiata is part... View all property information
    Make Enquiry
    Get the List
    From
    $913
    / Night
    View Details
    1 / 28
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    This spacious, stylishly furnished villa is set in extensive grounds, which offer a choice of venues for outdoor relaxation and dining. It is tucked away in a very secluded spot, amid gently rolling wooded hills. From its privileged hillside vantage point, it looks out across a valley covered in... View all property information
    Make Enquiry
    From
    $1,360
    / Night
    View Details
    1 / 55
    Poggio alle Mura
    5 Bedrooms / 5 Bathrooms / Sleeps 16
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fontanelle is without doubt one of our loveliest Tuscan properties. It is located to the west of Montalcino, an area renowned for its beauty and for its wines, especially the famous Brunello di Montalcino. The property is in a spectacular position, surrounded by vineyards, olive trees, cypresses... View all property information
    Make Enquiry
    From
    $12,062
    / Week
    Payment Protection
    View Details
    1 / 16
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Highlights Excellent furnished property set In a dominant position and close to the wonderful Castle of Velona, this property is on the top of a high hill overlooking the vineyards of Brunello. Historians will appreciate that its only 1 km from the magnificent abbey of Sant’Antimo. Independent... View all property information
    Make Enquiry
    From
    $1,573
    / Night
    View Details
    1 / 17
    6 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Villa Artista is a perfect place to enjoy a relaxing holiday, combining the atmosphere of typical Tuscan countryside with Montalcino's amenities. The villa is nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming pool, Jacuzzi, Turkish bath,... View all property information
    Make Enquiry
    From
    $14,976
    / Week
    View Details
    1 / 40
    Poggio alle Mura
    5 Bedrooms / 5 Bathrooms / Sleeps 16
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    [L A Y O U T] Ground Floor: Entrance hall; large beautifully furnished living room with fireplace and french windows opening onto the terrace and garden; covered dining terrace; dining room also opening to terrace; kitchen. In a separate wing, sitting room and, accessible through a staircase,... View all property information
    Make Enquiry
    From
    $135
    / Night
    View Details
    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    About this property
    Located in the Val d'Orcia region south of Siena. This area has been declared a world heritage site by UNESCO. The house is located on a hill with panoramic views over the countryside and only 2 mins from the village of Montisi. Sitting out on your terrazza overlooking your swimming pool soaking up... View all property information
    Make Enquiry
    From
    $820
    / Night
    View Details
    1 / 16
    4 Bedrooms / 4 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Charming and comfortable, villa Manfredi is an ideal spot for a relaxed getaway in the Val d’Orcia area of southern Tuscany. The quiet outdoor spaces and casual interiors of this four-bedroom stone villa invite you to spend lazy days at this home-away-from-home, but if you’d like to explore, it’s... View all property information
    Make Enquiry
    From
    $5,445
    / Night
    View Details
    1 / 15
    5 Bedrooms / 7 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy the privacy of your own Tuscan home combined with resort-worthy amenities at Casa Biondi. Located on the Castiglion del Bosco estate in the Val d’Orcia region, the five-bedroom property has space for a large family or group of friends, rustic charm to spare and an ideal location just steps... View all property information
    Make Enquiry
    From
    $4,622
    / Week
    View Details
    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Villa Antimo began life as a water mill in the 13th century. In 1606, the powerful Arrighi family enlarged the mill, which was fully functional until it was abandoned in 1945. The... View all property information
    Make Enquiry
    Enquire for rates
    1 / 24
    4 of 5 stars (2) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    It is a beautiful, bright and spacious villa and has been created in typical Tuscan style with traditional materials, including hand made terracotta floors, travertino stairs and kitchen surfaces and marble bathrooms. The villa has heating and air conditioning. The outdoor space includes a... View all property information
    Make Enquiry
    From
    $980
    / Week
    View Details
    1 / 23
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    'Vivo d'Orcia is not a place, it is a way of life...' The Castle of Vivo d'Orcia lies in the widespread Orcia valley in southern Tuscany, 2 hours from Florence, 1 hour from Siena, close to such cultural jewels as Pienza, Montalcino and Montepulciano, to name but a few. The hamlet lies at an... View all property information
    Make Enquiry
    From
    $3,403
    / Night
    View Details
    1 / 13
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Set on a hilltop next to the ruins of a medieval castle, Villa Castello offers a private, romantic retreat with panoramic views, intimate interiors and resort-worthy amenities. Three bedrooms make this restored farmhouse the perfect size for a family or a few couples, and its location on the... View all property information
    Make Enquiry
    From
    $4,765
    / Night
    View Details
    1 / 19
    5 Bedrooms / 6 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Set on the estate of Castiglion del Bosco in Tuscany’s Val d’Orcia region, Villa Stabbi pairs the charm of a traditional Tuscan country house with resort-worthy amenities and a stunning setting amid vineyards and a golf course. The property’s five bedrooms are divided between the main villa and a... View all property information
    Make Enquiry
    From
    $1,457
    / Night
    View Details
    1 / 23
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This villa provides guests with a panoramic pool, a living room, a fully equipped kitchen, a study room, four double bedrooms and three bathrooms. Additional amenities include: heating. View all property information
    Make Enquiry
    From
    $5,173
    / Night
    View Details
    1 / 18
    5 Bedrooms / 7 Bathrooms / Sleeps 9
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Expand your horizons at Villa Sant’Anna. The panoramic views from this restored farmhouse encompass the best of Tuscany’s Val d’Orcia region, from rolling hills and vineyards to a golf course, and five bedrooms provide plenty of space for the whole family or large groups of friends. A location on... View all property information
    Make Enquiry
    From
    $3,093
    / Week
    View Details
    1 / 44
    3 Bedrooms / 4 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    PRIVATE STRUCTURE. The villa is situated on an isolated hill, surrounded by the green Tuscan countryside, in the heart of the Val d'Orcia between San Quirico and Montalcino. Il Giardiniello is an old Leopoldino villa of unique architectural style, with the original structure dating to the 16th... View all property information
    Make Enquiry
    From
    $3,403
    / Night
    View Details
    1 / 12
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Once an olive-oil press for the estate of Castiglion del Bosco, Villa Oliviera has been converted to a charming three-bedroom escape for a family or a few couples. With stunning views of the area around Montalcino, breezy living spaces and quiet, private bedroom suites, the villa offers all the... View all property information
    Make Enquiry
    From
    $4,357
    / Night
    View Details
    1 / 17
    4 Bedrooms / 6 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    If spending the night in a former police station doesn’t appeal at first, the warm, elegant Villa Chiusa will change your mind. Four bedrooms divided between a main house and guest house offer plenty of space and privacy, and the property’s infinity pool wows with panoramic views of the countryside... View all property information
    Make Enquiry
    From
    $4,221
    / Night
    View Details
    1 / 17
    4 Bedrooms / 6 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    With the stone exterior of a traditional Tuscan farmhouse and rustic-chic interiors, Villa Gauggiole is a dreamy four-bedroom retreat in the Val d’Orcia region. Spread out over a main villa and guest house, the property offers plenty of space and privacy, but thanks to its location on the... View all property information
    Make Enquiry
    From
    $3,403
    / Night
    View Details
    1 / 13
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Perched on a hilltop and surrounded by gardens, Villa Alba is a quiet retreat in the heart of Tuscany’s Val d’Orcia region. Located on the Castiglion del Bosco estate, the three-bedroom villa is the perfect size for a family vacation, offering a private, luxurious space, resort-worthy amenities and... View all property information
    Make Enquiry
    From
    $1,565
    / Night
    View Details
    1 / 33
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Discover a lesser-known side of Tuscany at villa Pieve A Pava. Located in the Crete Senesi area just south of Siena, the six-bedroom property was once its own small borgo, but was recently converted to a luxury villa. Original stone walls, a small chapel and old ruins create a charming atmosphere... View all property information
    Make Enquiry
    From
    $1,781
    / Night
    View Details
    1 / 29
    9 Bedrooms / 9 Bathrooms / Sleeps 17
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Cozy up to villa Faggeto, a charming three-story home in Tuscany’s Val d’Orcia region. Situated among rolling hills near the town of Radicofani, the property offers quiet, beautiful grounds, a private tennis court and bright, luxuriously appointed interiors. Fill up the nine bedrooms with the whole... View all property information
    Make Enquiry
    From
    $2,326
    / Night
    View Details
    1 / 30
    7 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Sitting on a spectacular 25-acre estate and boasting stunning views of the hills of Montalcino, Villa Leopolda is a true gem of Tuscany's countryside. This remarkable 7-bedroom 7-bathroom property has been recently restored and tastefully furnished with a fine selection of antiques and exquisite... View all property information
    Make Enquiry
    From
    $1,457
    / Night
    View Details
    1 / 23
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Exteriors The fragrant smell of 10 hectares of vineyards and olive groves envelope this villa for rent in Tuscany, Italy, which at present shows its best face, thanks to the devoted restoration it underwent.From the panoramic pool guests will envisage before leaving on a walking tour the beauty... View all property information
    Make Enquiry
    From
    $6,399
    / Week
    View Details
    1 / 18
    6 Bedrooms / 6 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Villa San Giovese is a spacious luxury farmhouse, set among sweet rolling hills, extensive greens and wine producing vineyards in the Montalcino area, swimming pool and air conditioning Additional amenities include: heating. View all property information
    Make Enquiry
    From
    $6,405
    / Week
    View Details
    1 / 18
    12 Bedrooms / 11 Bathrooms / Sleeps 24
    Overview Make Enquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Pian Dell'asso is a beautiful, rustic Italian villa with a wide open lawn and spectacular interior furnishing. The furniture is elegant and comfortable, perfect for lounging about, reading, chatting, napping and setting the stresses of modern life aside.  The pool is particularly unique in its... View all property information
    Make Enquiry
    From
    $6,232
    / Week
    View Details
    1 / 19
    6 Bedrooms / 6 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Villa Artista is a perfect place to enjoy a relaxing holiday. It combines the atmosphere of typical Tuscan countryside with Montalcino's amenities. The villa is nestled just below Montalcino's historical centre, a peaceful spot with a large panoramic garden, swimming pool, Jacuzzi, Turkish bath,... View all property information
    Make Enquiry
    From
    $272
    / Night
    View Details
    1 / 19
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of... View all property information
    Make Enquiry
    From
    $313
    / Night
    View Details
    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    A few kilometers from Montalcino on the way to Castelnuovo Abate, in a finely renovated ancient stone farmhouse, five spacious apartments await you for your Tuscan vacation. All the apartments feature authentic period furnishings and modern amenities. Ville di Castelnuovo is situated at the top of... View all property information
    Make Enquiry
    Enquire for rates
    1 / 65
    15 Bedrooms / 15 Bathrooms / Sleeps 30
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    There are few vacation experiences that can prepare you for the splendor and magnificence of the imposing 11th century Castello and medieval borgo that surround it. The setting is simply magical, with incredible views of the Val di Chiana valley, overlooking vineyards, olive groves and cypress... View all property information
    Make Enquiry